Contact lens of high water content and high water balance

ABSTRACT

A contact lens of high water content and extremely high water balance made of a homopolymer or copolymer of 2,3-dihydroxypropyl methacrylate and methods of making such contact lenses, and polymers and hydrogels useful in such contact lenses.

BACKGROUND OF THE INVENTION

[0001] 1. Field of the Invention

[0002] The present invention relates to a contact lens formed from apolymer based on 2,3-dihydroxypropyl methacrylate (GMA) that has highwater content and high water balance. The present invention also relatesto methods of making and using such contact lenses. The presentinvention also relates to polymers and hydrogels of GMA and to methodsof making and using such polymers.

[0003] 2. Description of the Related Art

[0004] The literature teaches that high water content lenses aresusceptible to dimensional changes during wear is because they tend tolose a higher percent of water (dehydrate) relative to lenses of lowerwater content. Further, the ability to regain the lost water (rehydrate)is important to the dimensional stability of a contact lens. If a lensmaterial absorbs water more rapidly, then the lens will more closelyreturn to a water-saturated state during each blink, when the lens isbathed in tear fluid. Therefore, as a lens begins to dehydrate, acharacteristic of rapid rehydration is extremely advantageous formaintaining saturation and maximum stability.

[0005] Unfortunately, conventional contact lens development either hasignored the effect of rehydration rate upon lenses or has constructedlenses of materials with a less than optimal rate of rehydration.

[0006] U.S. Pat. No. 5,532,289, hereby incorporated by reference in itsentirety, describes a family of copolymers useful for making contactlenses. The copolymers have improved ability to remain near their watersaturated state during wear. In this patent, the inventors of thepresent invention describe a method for making contact lenses withimproved dimensional stability based on copolymers of2,3-dihydroxypropyl methacrylate (GMA) and 2-hydroxyethyl methacrylate(HEMA). The polymers contain between 20 and 90 mole percent of GMA andhave a water content from about 40 to about 70% by weight. Thedimensional stability of these lenses results from the ability of thesehydrogels to strongly bind water.

[0007] In the '289 patent, lenses made from this family of materialswere shown, under in-vitro conditions, to be slow to dehydrate and fastto rehydrate, relative to all other soft lens materials. The times ittook a lens to dehydrate to 10% of its water weight and rehydrate backto saturation were combined into a factor called “water balance”. This“water balance” value can be used to compare commercial lens materials,regardless of water content and as a guideline, by practitioners, inselecting an appropriate lens material for a patient. This patent alsoemphasizes the ability to remain near or at saturation as a key todimensional stability in a soft lens.

[0008] Clinical studies by Businger in Contact Lens Spectrum, August1995, pp. 19-25 and die Kontaklinsen 7-8, 4 (1997) support thelaboratory findings on water retention and lens stability. These studiesreport that lenses made from hioxifilcon A (p-GMA/HEMA, 59% water) werepreferred by the largest margin of test subjects because of comfort andvisual acuity. These lenses showed the highest dimensional stability andthe best of both low-contrast and high-contrast visual acuity duringwear cycles of 14 hours, over a period of 30 days, over otherconventional contact lenses irrespective of water content.

[0009] The literature teaches that the water content of GMA/HEMAcopolymers increases, from an initial 38% for p-HEMA, with increasingconcentration of GMA. See, Yasuda, et. al., Journal of Polymer Science:Part A1, 4, 2913-27 (1966) and Macret et. al., Polymer, 23(5) 748-753(1982), which describes hydrogels based on HEMA and GMA.

[0010] Refojo, Journal of Applied Polymer Science, 9, 3161-70 (1965),describes hydrogels of high water content made from GMA. The polymer aremade by polymerization in bulk or in water solution. Also, high watercontent hydrogels of copolymers of GMA and glycidyl methacrylate aredescribed.

[0011] Wichterle, et. al., UK Patent GB 2196973A, reported the use ofhydrophilic solvents, such as glycerol, dimethylformamide, anddimethylsulfoxide, in 2-HEMA blends primarily for the centrifugalcasting of contact lenses.

SUMMARY OF THE INVENTION

[0012] The literature is significantly void of examples of p-GMAhomopolymer and copolymers where the GMA content exceeds 80 molepercent, for use in contact lens application. While some of theliterature described above discusses hydrogels based on GMA polymers,the literature fails to suggests to fabricate contact lenses frompolymer of high GMA content; and certainly none of the literaturesuggests that contact lenses formed from polymers of at least 80 molepercent GMA could exhibit the outstanding and unexpected properties,including slow dehydration and fast rehydration, i.e., a high waterbalance, discovered by the present inventors.

[0013] Since polymers that contain 2;3-dihydroxypropyl methacrylate(GMA) show improved water retention capability (See Pescossolido et al.,Contactologia, 15D, 64-7 (1993) and Benz et al., Contact Lens SpectrumJuly 1997, pp. 40-46), the present inventors conceived that a polymercomposed mostly of GMA should yield a contact lens with extraordinarydimensional stability and water retention. Overall lens performance,with respect to stability and water retention, should surpass anycommercial available lens material. However, to date, the art has failedto suggest contact lenses formed of polymers having at least 80 molpercent GMA or method of making such lenses.

[0014] Accordingly, it is an object of the present invention to providecontact lenses formed from a material primarily composed of GMA.

[0015] It is also an object of the invention to provide methods ofmaking and using such contact lenses.

[0016] Another object of the invention is to provide polymers withimproved machining, useful for a spheric contact lens, a toric contactlens, a multifocal contact lens, and a bandage contact lens.

[0017] Another object of the invention is to provide a spheric contactlens, a toric contact lens, a multifocal contact lens, and a bandagecontact lens with superior dimensional stability.

[0018] Another object of the invention is to provide a spheric contactlens, a toric contact lens, a multifocal contact lens and a bandagecontact lens with superior water retention and water balance.

[0019] Another object of the invention is to provide a spheric contactlens, a toric contact lens, a multifocal contact lens and a bandagecontact lens suitable for daily wear and extended wear modalities.

[0020] It is also an object of the invention to provide blanks forcontact lenses, and finished and unfinished contact lenses havingimproved characteristics, such as high water content and high waterbalance.

[0021] In accordance with these and other objectives, there has beenprovided according to the present invention, a contact lens formed of acopolymer of more than 80 mole percent, generally more than 90 molpercent, of 2,3-dihydroxypropyl methacrylate and up to 20 mol percent,generally from 0.05 up to 10 mol percent of a reactive pyrollidone, suchas a N-alkenyl pyrolidone, such as N-vinyl pyrolidone, or alkoxy alkylmethacrylate of formula R₁—O—R₂—MA, wherein R₁ and R₂ are independentlyalkyl groups of 1 to 6 carbon atoms, and MA is methacrylate.

[0022] There also has been provided in accordance with the presentinvention, a hydrogel of a polymer including more than 90 mole percentof units from 2,3-dihydroxypropyl methacrylate and up to 10 mol percentof N-vinyl pyrolidone or alkoxy alkyl methacrylate of formulaR₁—O—R₂—MA, wherein R₁ and R₂ are independently alkyl groups of 1 to 6carbon atoms and MA is methacrylate, wherein the polymer has a watercontent of at least 60% by weight of the polymer.

[0023] There is also provided a contact lens formed from a homopolymerof 2,3-dihydroxypropyl methacrylate, wherein the polymer has a watercontent of at least 60%, and a water balance of greater than about 8relative to that of p-HEMA.

[0024] There is also provided in accordance with the present invention amethod of making a polymer including more than 90 mol percent of unitsfrom 2,3-dihydroxypropyl methacrylate, comprising polymerizing2,3-dihydroxypropyl methacrylate in the presence of a polar aproticdiluent.

[0025] There is also provided a method of making a contact lens,comprising polymerizing GMA and a comonomer in the presence of a polaraprotic diluent to form a copolymer, and forming the copolymer into acontact lens.

[0026] Further objects, features, and advantages of the presentinvention will become apparent from the detailed description ofpreferred embodiments that follows.

BRIEF DESCRIPTION OF THE FIGURES

[0027]FIG. 1 shows the viscosity variation for blends of 2-HEMA with GMAand NVP.

[0028]FIG. 2 shows the viscosity of GMA in various diluents.

[0029]FIG. 3 shows the viscosity of GMA in various diluents.

DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS

[0030] The present invention provides a family of non-ionic, high watercontent materials with excellent dimensional stability, high waterbalance, and improved lathing (machinability), useful in making contactlenses. The material is a homopolymer or copolymer (containing 2 or moretypes of monomers), having more than 80 mole percent, preferably morethan 90 mol percent of GMA. The homopolymer include about 100 molpercent of the GMA. Useful comonomers polymerizable with the GMA includeany comonomers that can be polymerized with GMA.

[0031] The homopolymers and copolymers of the invention generally have awater content of at least about 60 percent, such as greater than about65%, or greater than about 70% by weight. They also have a water balancerelative to that of p-HEMA of greater than about 8, generally greaterthan 9, and even greater than 10. Water balance is described in U.S.Pat. No. 5,532,289 and application Ser. No. 08/674,275 filed Jul. 1,1996, both hereby incorporated by reference in their entireties.

[0032] The polymers of the present invention can be formed intohydrogels, contact lens blanks, semi-finished contact lenses, orfinished contact lenses. The contact lenses can be of any type includingspheric, toric, multifocal, and bandage contact lenses.

[0033] The present inventors have found that alkoxy-alkylmethacrylatesof formula R₁—O—R₂—MA, wherein R₁ and R₂ are independently alkyl groupsof 1 to 6 carbon atoms, and MA is methacrylate; and reactivepyrolidones, such as N-vinyl pyrollidone are especially usefulcomonomers.

[0034] The polymers of GMA can be prepared using polymerizationtechniques well known to those in the art. Any desired crosslinkingagents or initiators can be used in result-effective amounts. Usefulcrosslinking agents include ethylene glycol dimethacrylate. Crosslinkersare generally used in amounts of less than 5 weight percent, generallyless than 2 weight percent, based on the weight of the polymer. Usefulinitiators include the azo initiators such as used in the examples.Polymerization can takes place at any temperature, but preferably aboveroom temperature, for example, above 30° C. or above about 40° C.

[0035] Due to the fact that concentrated GMA solutions are highlyviscous, the present inventors have also developed a procedure forpreparing polymers having a high content of GMA. As with glycerol, GMA'shigh viscosity results in part because of the vicinal —OH groups leadingto a tight (hydrogen-bond) network, which greatly influencepolymerization because molecular motion is greatly restricted.

[0036] The effect of GMA on viscosity can be seen in FIG. 1. FIG. 1shows the contrasting effect on the viscosity of 2-HEMA when blendedwith monomers like GMA and NVP. Addition of GMA increases the viscosityof the HEMA blend, while NVP has the opposite effect. NVP reduces theviscosity of HEMA blends, in part, because it contains no hydroxylgroups (i.e., is aprotic) and disrupts the internal H-bond network sincethe lactam nitrogen is a weaker hydrogen-bonding moiety. When GMA ispolymerized in the presence of NVP, the disruption of the intermolecularH-bond network of the GMA, reduces viscosity and improves thepolymerization conditions and consistency. During the initial phase ofthe polymerization with GMA, the NVP comonomer acts as a reactivediluent improving the mobility of the di-hydroxy containing comonomerand allowing a higher level of polymerization prior to gel.

[0037] Thus, the present invention relates to method of preparing GMApolymers by polymerizing in the presence of a reactive polar aproticdiluent, such as N-vinyl pyrollidone and/or a non-reactive polar aproticdiluent. Protic diluents can be used in combination with the aproticdiluents. Generally, at least 50% by weight of the total diluent shouldbe an aprotic polar diluent, which is reactive or unreactive.

[0038] As discussed above, the present invention relates to GMAhomopolymers and copolymers, useful in contact lenses. The homopolymersand copolymers are discussed below.

[0039] GMA Homopolymer:

[0040] To obtain a GMA homopolymer, the GMA is combined with one or morenon-reactive polar aprotic diluents or blend of such diluents with aprotic diluent and polymerized. Non-reactive diluents are ones that donot copolymerize with the GMA, thus ensuring that a homopolymer of GMAis formed. The non-reactive polar diluent (s) act to disrupt theintra-intermolecular H-bond network of the GMA monomer and to reduce theviscosity of the blend, thereby increasing reactant mobility andallowing a more desirable and random polymerization. Diluent selectionis important because it should be inert, should improve thepolymerization process, and should be effectively removed duringhydration.

[0041] Two fundamental types of diluent that can be used inpolymerizations are protic and aprotic diluents. An aprotic diluent isused in the methods of the present invention. Polar aprotic diluentsalone or in combination with protic diluents, such as water can be used.

[0042]FIGS. 2 and 3 show the viscosity of GMA with various diluents.Protic diluents are diluents with hydroxyl groups available forH-bonding, and include water, ethylene glycol (EG), and blends thereof.These diluents modify viscosity and affect the GMA hydrogen bond networkbut can also strongly contribute to the H-bond network. Aprotic diluentsare diluents without hydrogen moieties available for H-bonding, such asN-methyl pyrrolidone (NMP), N,N-dimethylformamide (DMF), tetrahydrofuran(THF), and the like. The aprotic diluents are preferably polar. Theaprotic diluents can more effectively disrupt the hydrogen bond networkwhile contributing weakly to the network and reducing the viscosity ofthe GMA monomer. Thus, polar aprotic diluents, such as NMP, are used inthe present invention. But again, protic diluents can be combined withthe aprotic diluents. In addition to NMP and NVP, any alkyl, or alkenylN-substituted lactam can be used as polar aprotic diluent.

[0043]FIGS. 2 and 3 show the reduction in GMA viscosity, over a range oftemperatures, brought about by blending the GMA monomer with bothnon-reactive diluents, such as NMP and EG, and reactive polar diluents,such as HEMA and NVP. FIGS. 2 and 3 also show that, as expected,differences in the viscosity of the blends decrease with temperature. Toapproach a viscosity range (<20 cps) like that for HEMA, at roomtemperature, diluent amounts greater than 15 weight % are generallyneeded. However, at temperatures above 45° C. the differences inviscosity of the various blends decrease allowing for lowerconcentration of diluent.

[0044] GMA Copolymers & Terpolymers:

[0045] In addition to GMA homopolymer, the present invention relates toGMA copolymers and terpolymers. The inventors have developed an approachto achieve a high water content in a hydrogel primarily composed of GMA.This approach is to combine the GMA with either a monomer or blend ofmonomers that also act as a diluent during polymerization to change theintra-intermolecular H-bond network of the GMA monomer and modify theviscosity of the mixture to allow a high degree of cure prior to gel.The copolymer or terpolymers generally have more than about 80 molpercent of GMA, preferably more than 90 mol percent GMA, for example,they are composed of 90 to 99 mole % GMA. The comonomers can be presentin amounts of up to 20 mol percent, for example from 0.05 to 20 molpercent, or from 0.5 to 10 mol percent or 1 to 8 mole %.

[0046] Any comonomer or mixture of comonomers polymerizable with GMA canbe used, so long as the resulting copolymer/terpolymer has physical,optical and machining characteristics suitable for contact lenses. Theterm copolymers means polymers of at least two monomers, includingterpolymers of three monomers, and polymers formed from more than threemonomers.

[0047] Useful comonomers include pyrrolidone derivative like NVP(N-vinyl pyrrolidone) and alkoxy alkyl methacrylates of the formulaR₁—O—R₂—MA, where R₁ is an alkyl group having 1 to 6, preferably 1-4,carbon atoms such as methyl, ethyl, n-propyl, n-butyl and R₂ is an alkylgroup having 1 to 6, preferably 1-4, carbon atoms such as ethyl andpropyl, and MA is methacrylate.

[0048] Additions of N-vinylpyrrolidone (NVP) andalkoxy-alkyl-methacrylates like ethoxy ethyl methacrylate (EOEMA)provide improved machinability while maintaining the high water contentand water balance values of the copolymers. During polymerization toproduce the copolymers, the viscosity of the monomer blends can befurther optimized by the inclusion of protic or aprotic diluents such asNMP, EG, or water. During polymerization, a reactive and/or non-reactiveaprotic diluent should be used. NMP and NVP modify the viscosity andenhance the mixture reactivity (See Kloosterboer et. al., Phillips Tech.Rev., 40, 298 (1982)). The EOEMA also modifies the viscosity of theblend improving reactant mobility.

[0049] Contact lens blanks, semi-finished lenses, and contact lenses canbe prepared from the GMA homo- and copolymers of the present inventionusing techniques well know to those in art. See, for example, U.S. Pat.No. 5,532,2890, herein incorporated by reference in its entirety.

[0050] The contact lenses of the present invention have low proteinbuild-up, a high water balance (low rate of water evaporation and highrate of rehydration) and substantially less tendency to desiccate thecornea of extended wear soft lens patients. Due to the use of a polaraprotic diluent(s) during polymerization, water contents of above 70% orabove 72 or 74% can be obtained. UV absorbing monomer(s) andtint-forming pigment(s) can be used in manufacturing the contact lens aswould be understood by those in the art. The invention is illustrated bythe following examples, which illustrate the invention, but do not limitit.

EXAMPLE 1

[0051] Preparation of GMA Homopolymer with 74% Water Content

[0052] 91.7 grams of GMA were mixed with 8.2 grams of NMP and 0.03 gramsof cyclohexanecarbonitrile, 1,1′-azobis initiator. The total diesterconcentration was adjusted to 0.07% by weight with ethylene glycoldimethacrylate (EGDMA). The mixture was degassed while applying vigorousstirring. The mixture was dispensed into cylindrical molds, polymerizedat 50° C. for 10 hours, and post-cured at 100° C. for 5 hours. Thepolymer was then removed from the molds and formed into contact lensbuttons (blanks). The mechanical formation process comprised cutting thepolymer into cylinders of 0.5 to 0.65 inches (1.27 to 1.65 cm.) indiameter and 0.1 to 0.2 inches (0.25 to 0.51 cm.) in thickness. Theblanks were further cured at 100° C. for 5 hours. After curing, the flatparallel faces of the buttons (blanks) were ground perpendicular to thecylinder walls with the desired dimensions.

EXAMPLE 2

[0053] Preparation of GMA/NVP Copolymer with 69% Water Content

[0054] 91.8 grams of GMA were mixed with 3.4 grams of NVP and 4.8 gramsof water. To the mixture, 0.03 grams of2,2-azobis(2,4-dimethylvaleronitrile) were added and the total diesterconcentration adjusted to 0.3% by weight with ethylene glycoldimethacrylate (EGDMA). The mixture was degassed while applying vigorousstirring. The mixture was dispensed into cylindrical molds, polymerizedat 30° C. for 10 hours, and post-cured at 100° C. for 5 hours. Thepolymer was then removed from the molds and formed into contact lensblanks. The mechanical formation process included cutting the polymerinto cylinders of 0.5 to 0.65 inches (1.27 to 1.65 cm.) in diameter and0.1 to 0.2 inches (0.25 to 0.51 cm.) in thickness. The blanks werefurther cured at 100° C. for s hours. The polymer was then removed fromthe molds and formed into contact lens blanks as described previously.

EXAMPLE 3

[0055] Preparation of GMA/NVP Copolymer with 74% Water Content

[0056] 90.1 grams of GMA were mixed with 3.3 grams of NVP and 6.5 gramsof NMP. To the mixture 0.03 grams of cyclohexanecarbonitrile,1,1′-azobis were added. The total diester concentration was adjusted to0.08% by weight with ethylene glycol dimethacrylate (EGDMA). The mixturewas degassed while applying vigorous stirring. The mixture was dispensedinto cylindrical molds, polymerized at 50° C. for 10 hours, andpost-cured at 100° C. for 5 hours. The polymer was then removed from themolds and formed into contact lens blanks as described in Example 1.

EXAMPLE 4

[0057] Preparation of GMA/NVP Copolymer

[0058] 90.1 grams of GMA were mixed with 3.3 grams of NVP and 6.5 gramsof DMF. To the mixture 0.03 grams of cyclohexanecarbonitrile,1,1′-azobis were added. The total, diester concentration was adjusted to0.07% by weight with ethylene glycol dimethacrylate (EGDMA). The mixturewas degassed while applying vigorous stirring. The mixture was dispensedinto cylindrical molds, polymerized at 50° C. for 10 hours, andpost-cured at 100° C. for 5 hours. The polymer was then removed from themolds and formed into contact lens blanks as described in Example 1.

EXAMPLE 5

[0059] Preparation of GMA/NVP Copolymer

[0060] 90.1 grams of GMA were mixed with 3.3 grams of NVP and 6.5 gramsof ethylene glycol. To the mixture 0.03 grams ofcyclohexanecarbonitrile, 1,1′-azobis were added. The total diesterconcentration was adjusted to 0.07% by weight with ethylene glycoldimethacrylate (EGDMA). The mixture was degassed while applying vigorousstirring. The mixture was dispensed into cylindrical molds, polymerizedat 50° C. for 10 hours, and post-cure at 100° C. for 5 hours. Thepolymer was then removed from the molds and formed into contact lensblanks as described in Example 1.

EXAMPLE 6

[0061] Preparation of GMA/EOEMA Copolymer with 72% Water Content

[0062] 89.6 grams of GMA were mixed with 4.6 grams of EOEMA and 5.7grams of NMP. To the mixture 0.03 grams of cyclohexanecarbonitrile,1,1′-azobis were added and the total diester concentration adjusted to0.07% by weight with ethylene glycol dimethacrylate (EGDMA). The mixturewas degassed while applying vigorous stirring. The mixture was dispensedinto cylindrical molds, polymerized at 50° C. for 10 hours, andpost-cured at 100° C. for 5 hours. The polymer was then removed from themolds and formed into contact lens blanks as described in Example 1.

EXAMPLE 7

[0063] Preparation of GMA/NVP Copolymer with 74% Water Content

[0064] 90.1 grams of GMA were mixed with 3.3 grams of NVP and 6.5 gramsof NMP. To the mixture, 0.03 grams of cyclohexanecarbonitrile,1,1′-azobis were added. The total diester concentration was adjusted to0.07% by weight with ethylene glycol dimethacrylate (EGDMA). The mixturewas degassed while applying vigorous stirring. The mixture was dispensedinto cylindrical molds, polymerized at 50° C. for 10 hours, andpost-cured at 100° C. for 5 hours. The polymer was then removed from themolds and formed into contact lens blanks as described in Example 1.

EXAMPLE 8

[0065] Preparation of GMA/NVP/EOEMA Terpolymer with 73% Water Content

[0066] 87.0 grams of GMA were mixed with 3.3 grams of NVP, 2.0 grams ofEOEMA and 6.5 grams of NMP. To the mixture, 0.03 grams ofcyclohexanecarbonitrile, 1,1′-azobis were added and the total diesterconcentration was adjusted to 0.08% by weight with ethylene glycoldimethacrylate (EGDMA). The mixture was degassed while applying vigorousstirring. The mixture was dispensed into cylindrical molds, polymerizedat 50° C. for 10 hours, and post-cured at 100° C. for 5 hours. Thepolymer was then removed from the molds and formed into contact lensblanks as described previously.

[0067] The formulations for Examples 1-8 are summarized in Table 1. Theproperties are set out in Table 2. TABLE 1 Chemical Composition inWeight Percent EXAMPLE EXAMPLE 1 EXAMPLE 2 EXAMPLE 3 EXAMPLE 4 EXAMPLE 5EXAMPLE 6 7 EXAMPLE 8 2,3-DHPMA 91.7 91.8 90.1 90.1 90.1 89.6 90.1 87(GMA) EOEMA — — — — — 4.6 2 NVP — 3.4 3.3 3.3 3.3 — 3.3 3.3 Initiator0.03 0.03 0.03 0.03 0.03 0.03 0.03 0.03 VAZ0 52/64/88 EGPMA 0.07 — 0.080.07 0.07 0.08 0.07 0.08 NON-REACTIVE DILUENTS Protic — 4.8 — — 6.5 — —— DI-H₂O EG Aprotic 8.2 — 6.5 6.5 — 5.7 6.5 6.5 NMP NMP DMF NMP NMP NMP

[0068] TABLE 2 Material Properties EXAMPLE PROPERTY EXAMPLE 1 EXAMPLE 2EXAMPLE 3 EXAMPLE 4 EXAMPLE 5 EXAMPLE 6 7 EXAMPLE 8 Water 74 69 74 NotNot 72 74 73 Content (%) Measured Measured Water 15 8 11 Not Not Not 88.5 Balance Measured Measured Measured (Relative to 2-HEMA) Linear 1.6121.541 1.624 Not Not Not 1.628 1.617 Expansion Measured Measured MeasuredRadial 1.620 1.541 1.628 Not Not Not 1.628 1.619 Expansion MeasuredMeasured Measured Hardness 87 76 87 70 64 85 85 88 (Shore D)Transmission >96 >97 >98 Not Not Not >98 >98 (%) at 600 MeasuredMeasured Measured nm

[0069] The Water Balance was determined as follows

[0070] 1. Purpose:

[0071] The purpose of this test was to determine the water balancecapability of the hydrogel lenses using gravimetric techniques. Waterbalance is defined as the ratio of the time it takes a lens to dehydrateby 10% of its water weight and the time it takes to return tosaturation. Values are reported relative to p-HEMA (Polymacon, 38%),used as a control.

[0072] It is important that ambient conditions for the test bemaintained accurately, and that all samples be measured under the samecontrolled conditions. The specified conditions are 21°±2° C. and 40±5%RH.

[0073] 2. Test Equipment:

[0074] High precision, calibrated balance (such as Sartorius, Mettler,etc.) with 0.0001 gram capability. The balance should be placed in acontrolled temperature and relative humidity environment of 21° C.±2°and 40±5% relative humidity.

[0075] 3. Fabrication of Sample Lenses:

[0076] For each material, uniform thickness lenses were based onexpansion factors to yield a final wet (uniform) thickness lens of 0.1mm. Finished dry lenses were cleaned and hydrated overnight in bufferedsaline solution. BENZ buffered saline solution is composed of 8.01 gramsNaHBO₃, 2.47 grams of H₃BO₃, and 0.14 grams Na₂B₄O₇:10H₂O in 1 liter ofdistilled water, with a pH=7.26 and an osmolarity of 295 mOs at 22.5° C.

[0077] 4. Lens Dehydration Procedure.

[0078] Remove a clean sample lens from saline vial, secure lens on wireholder and blot gently with a lint free paper. Hang the wire holder on abalance scale, weigh and record weight. Dehydrate the lens by 10% of itstotal water weight, recording the weight and cumulative time every 20seconds until the 10% weight loss is achieved. After the test iscomplete, return the lens to the saline flask, allow the lens torehydrate back to saturation and repeat the drying procedure at least 2more times to obtain an average weight loss.

[0079] 5. Lens Rehydration Procedure.

[0080] Remove a clean sample lens from saline vial, secure lens on wireholder and blot gently with a lint free paper. Hang the wire holder onthe balance scale and weigh the lens to determine the weight of thesaturated lens. Record the weight. Allow the lens to dehydrate 10% ofits water weight (saturated weight×water content×10%). Record weight.Remove wire-holder from the scale and submerge the lens in bufferedsaline for 10 seconds. Remove the lens from the saline, blot gently witha lint free paper and weigh the lens. Record the weight and timehydrated. After weight is recorded, re-submerge the lens 10 moreseconds. Blot and record the weight and cumulative time hydrated.Continue this procedure until the saturated weight of the lens isachieved. Repeat complete procedure 3 times to obtain an average weightgain.

[0081] 6. Results:

[0082] The water balance ratio of a material is obtained by dividing thetime (in minutes) to dehydrate 10% from saturation by the time (inminutes) to rehydrate from 90% of saturation. This ratio value is thecompared to p-HEMA control.

[0083] With the exception of Example 2 (69%), all examples show a watercontent higher than 70% and relative water balance values higher thanp-GMA/2-HEMA (69% water described in U.S. Pat. No. 5,532,289).

[0084] The contact lenses of the present invention have unexpectedlyhigh water balance, i.e., of greater than about 8. This high waterbalance was quite unexpected and found by the present inventors onlyafter fabrication of contact lenses from the described GMA materials.Contact lenses formed from the materials of the invention offer numerousimprovements, including: high water balance, high water content,reduction of opacity in the lenses, ease of lenses machining, andincreased material strength.

[0085] While several embodiments of the invention have been described,it will be understood that it is capable of further modifications, andthis application is intended to cover any variations, uses, oradaptations of the invention, following in general the principles of theinvention and including such departures from the present disclosure asto come within knowledge or customary practice in the art to which theinvention pertains, and as may be applied to the essential featureshereinbefore set forth and falling within the scope of the invention orthe limits of the appended claims.

What is claimed is:
 1. A contact lens formed of a copolymer formed frommore than about 80 mole percent of 2,3-dihydroxypropyl methacrylate andfrom about 0.05 to about 20 mol percent of more or more of a N-alkenylpyrolidone or alkoxy alkyl methacrylate of formula R₁—O—R₂-MA, whereinR₁ and R₂ are independently alkyl groups of 1 to 6 carbon atoms, and MAis methacrylate.
 2. A contact lens according to claim 1, wherein thecopolymer has a water content of at least about 60% by weight of thepolymer, and wherein the copolymer has at least about 90 mole percent of2,3-dihydroxypropyl methacrylate.
 3. A contact lens according to claim1, which is non-ionic and has a water balance of more than about 8relative to poly-2 hydroxyethyl methacrylate.
 4. A contact lensaccording to claim 1, wherein the copolymer has a water content of morethan about 65% by weight.
 5. A contact lens according to claim 1,wherein the copolymer has a water content of more than about 70% byweight.
 6. A contact lens according to claim 1, wherein the copolymercontains about 0.5 to 10 mole percent of said pyrolidone or said alkoxyalkylmethacrylate.
 7. A contact lens according to claim 1, wherein thecopolymer is a copolymer of 2,3-dihydroxypropyl methacrylate and N-vinylpyrolidone.
 8. A contact lens according to claim 1, wherein thecopolymer is a copolymer of 2,3-dihydroxypropyl methacrylate and saidalkoxy alkyl methacrylate.
 9. A contact lens according to claim 8,wherein the alkoxy alkylmethacrylate comprises ethoxy ethylmethacrylate.10. A hydrogel having a water content of at least about 60% by weight ofthe polymer formed from more than about 80 mole percent of2,3-dihydroxypropyl methacrylate and from about 0.05 to about 20 molpercent of N-vinyl pyrolidone or alkoxy alkyl methacrylate of formulaR₁—O-13 R₂-MA, wherein R₁ and R₂ are independently alkyl groups of 1 to6 carbon atoms and MA is methyacrylate.
 11. A contact lens formed of apolymer formed from more than about 92 mole percent of2,3-dihydroxypropyl methacrylate, wherein the polymer has a watercontent of at least about 60% by weight of the polymer.
 12. A contactlens according to claim 11, which is a homopolymer of2,3-dihydroxypropylene methacrylate and which has a water balance ofmore than about 8 relative to poly-2-hydroxyethyl methacrylate.
 13. Amethod of making a polymer including more than 90 mol percent of unitsfrom 2,3-dihydroxypropyl methacrylate, comprising polymerizing2,3-dihydroxypropyl methacrylate in the presence of a reactive ornon-reactive polar aprotic diluent.
 14. A method according to claim 13,wherein the polar aprotic diluent comprises N-methyl pyrollidone,N,N-dimethylformamide, or tetrahydrofuran.
 15. A method according toclaim 13, wherein the polymer is a homopolymer of said2,3-dihydroxypropyl methacrylate.
 16. A method according to claim 13,wherein the polymer is a copolymer of said 2,3-dihydroxypropylmethacrylate and N-vinyl pyrolidone or alkoxy alkyl methacrylate offormula R₁—O—R₂-MA, wherein R₁ and R₂ are independently alkyl groups of1 to 6 carbon atoms, and MA is methacrylate.
 17. A method of making acontact lens according to claim 1, comprising polymerizing the monomersin the presence of a reactive or non-reactive polar aprotic diluent toform said copolymer, and forming said co-polymer into a contact lens.18. A method according to claim 17, wherein the polymerization takesplace in the presence of a non-reactive aprotic diluent
 19. A method ofmaking a contact lens, comprising polymerizing 2,3-dihydroxypropylmethacrylate in the presence of a reactive or non-reactive polar aproticdiluent to form a polymer having more than 90 mol percent of units from2,3-dihydroxypropyl methacrylate, and forming said polymer into acontact lens.
 20. A method according to claim 16, wherein the polymer isa homopolymer of 2,3-dihydroxypropyl methacrylate and the diluentcomprises an alkyl or alkenyl N-substituted lactam.